IP Library Granted Patent US 10,357,445
Granted Patent B2
US 10,357,445 · App. 15/306,186 · Granted Jul 23, 2019

Cross-linked composition and cosmetic composition comprising the same

Inventors: Mary Kay Crofoot (Midland, MI); Roxanne Haller (Saginaw, MI); Donald Anthony Kadlec (Midland, MI); Kimmai Thi Nguyen (Midland, MI); Kenneth Edward Zimmerman (Midland, MI)
Assignee: Dow Silicones Corporation
A61K8/891A61K8/8147A61K8/894A61Q1/06A61Q5/00A61Q5/02A61Q5/12A61Q15/00A61Q19/00A61Q19/10C08G77/38C08K5/01C08K5/092C08K5/56C08L83/06A61K2800/10A61K2800/594C08G77/12C08G77/14
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Quick Facts
Patent No.
US 10,357,445
App. No.
15/306,186
Granted
Jul 23, 2019
Kind
B2
Abstract

A cross-linked composition comprises the reaction product of an organohydrogensiloxane and a cross-linker, in the presence of a hydrosilylation catalyst. The organohydrogensiloxane comprises siloxy units of average formula (I): (R 4 3 SiO 1/2 )(R 4 2 —SiO 2/2 ) a (R 1 R 4 SiO 2/2 ) b (R 4 HSiO 2/2 ) c (R 2 R 4 SiO 2/2 ) d (R 3 R 4 SiO 2/2 ) e —(R 4 3 Si—O 1/2 ). Each of R 1 and R 2 is an independently selected hydrogen atom or a substituted or unsubstituted hydrocarbyl group. R 3 is a hydrogen atom or a group having at least one carboxyl group or a precursor thereof. R 4 is an independently selected substituted or unsubstituted hydrocarbyl group. Further, a≥0, b≥0, c≥1, d≥0, and e≥1. The cross-linker has at least two aliphatic unsaturated hydrocarbon groups. A method of forming the cross-linked composition comprises the steps of providing the organohydrogensiloxane and cross-linker, and combining the organohydrogensiloxane and cross-linker in the presence of the hydrosilylation catalyst to form the cross-linked composition. A cosmetic composition is provided that includes the cross-linked composition and at least one cosmetic component.

Claims (42)

1. A cross-linked composition comprising the reaction product of:

A) an organohydrogensiloxane comprising siloxy units of average formula (I);

(R 4 3 SiO 1/2 )(R 4 2 SiO 2/2 ) a (R 1 R 4 SiO 2/2 ) b (R 4 HSiO 2/2 ) c (R 2 R 4 SiO 2/2 ) d (R 3 R 4 SiO 2/2 ) e —(R 4 3 Si—O 1/2 )

 where each of R 1 and R 2 is an independently selected hydrogen atom or a substituted or unsubstituted hydrocarbyl group, R 3 is a group having at least one carboxyl group or a precursor thereof selected from an anhydride group and a capped carboxyl group, each R 4 is an independently selected substituted or unsubstituted hydrocarbyl group, a≥0, b≥0, c≥1, d≥0, and e≥1; and

B) a cross-linker having at least two aliphatic unsaturated hydrocarbon groups;

in the presence of

a hydrosilylation catalyst.

2. A cosmetic composition comprising:

(I) a cross-linked composition; and

(II) at least one cosmetic component;

optionally in a cosmetically acceptable medium;

wherein the cross-linked composition is as set forth in claim 1 .

3. The composition as set forth in claim 1 , wherein said cross-linked composition comprises the further reaction product of C2) water, an alcohol, or a combination thereof.

4. The composition as set forth in claim 1 , wherein component B) is of formula (III): R 5 —Y—R 5 ; where R 5 is a monovalent unsaturated aliphatic hydrocarbon group having 2 to 12 carbon atoms and Y is a divalent organic group, divalent siloxane group, or divalent organosiloxane group.

5. The composition as set forth in claim 1 , said cross-linked composition being of the following general formula (II):

where W is a divalent group, each of R 1 , R 1′ , R 2 , R 2′ , R 4 , and R 4′ is an independently selected substituted or unsubstituted hydrocarbyl group, each of R 3 and R 3′ is independently a group having at least one carboxyl group or a precursor thereof, a≥0, a′≥0, b≥0, b′≥0, c≥1, c′≥1, d≥0, d′≥0, e≥1, and e′≥1.

6. The composition as set forth in claim 1 , wherein:

i) R 3 has a terminal carboxyl group; or

ii) R 3 has a terminal carboxyl group precursor selected from an anhydride group or a capped carboxyl group; or

iii) R 3 is a derivative of allyl succinic anhydride (ASA) or trimethylsilyl undecylenate.

7. The composition as set forth in claim 1 , wherein:

i) the sum of a+b+c+d+e is an integer selected from 4 to 2,000; and/or

ii) 10≤a≤500, 0≤b≤100, 1≤c≤100, 0≤d≤100, and 1≤e≤100; and/or

iii) R 1 is a methyl group, R 2 is an aliphatic or aromatic group having from 1 to 12 carbon atoms, and R 4 is R 1 .

8. A method of forming a cross-linked composition, said method comprising the steps of:

providing A) an organohydrogensiloxane comprising siloxy units of average formula (I);

(R 4 3 SiO 1/2 )(R 4 2 SiO 2/2 ) a (R 1 R 4 SiO 2/2 ) b (R 4 HSiO 2/2 ) c (R 2 R 4 SiO 2/2 ) d (R 3 R 4 SiO 2/2 ) e —(R 4 3 Si—O 1/2 )

where each of R 1 and R 2 is an independently selected hydrogen atom or a substituted or unsubstituted hydrocarbyl group, R 3 is a group having at least one carboxyl group or a precursor thereof selected from an anhydride group and a capped carboxyl group, each R 4 is an independently selected substituted or unsubstituted hydrocarbyl group, a≥0, b≥0, c≥1, d≥0, and e≥1;

providing B) a cross-linker having at least two aliphatic unsaturated hydrocarbon groups; and

combining components A) and B) in the presence of a hydrosilylation catalyst to form the cross-linked composition;

wherein the cross-linked composition is at set forth in claim 1 .

9. The method as set forth in claim 8 , further comprising the steps of:

providing D) water, an alcohol, or a combination thereof; and

reacting the cross-linked composition and component D) to further form the cross-linked composition.

10. The method as set forth in claim 8 , further comprising the step of:

providing C2) water, an alcohol, or a combination thereof; and

reacting R 3 and component C2) to further form the cross-linked composition.

11. The composition as set forth in claim 3 , wherein R 3 is a derivative of allyl succinic anhydride (ASA).

12. The composition as set forth in claim 3 , wherein R 3 is a derivative of trimethylsilyl undecylenate.

13. The method as set forth in claim 10 , wherein R 3 is a derivative of allyl succinic anhydride (ASA) or trimethylsilyl undecylenate.

14. The cosmetic composition as set forth in claim 2 , further defined as a personal care composition and/or a composition for the care of keratinous substrates.

15. The cosmetic composition as set forth in claim 2 , wherein the cosmetically acceptable medium is present.

Assignments (2)
CHANGE OF NAME Recorded Feb 28, 2018
From: DOW CORNING CORPORATION
To: DOW SILICONES CORPORATION
Reel/Frame 045470/0188 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 24, 2016
From: CROFOOT, MARY KAY; HALLER, ROXANNE; KADLEC, DONALD ANTHONY; NGUYEN, KIMMAI THI; ZIMMERMAN, KENNETH EDWARD
To: DOW CORNING CORPORATION
Reel/Frame 040101/0572 →
Continuity (3)
Provisional Application 61984966 · Apr 28, 2014
Provisional Application 62017570 · Jun 26, 2014
Related Publication 20170065514A1 · Mar 9, 2017